Penicillins and cephalosporins are β-lactam antibiotics which are most widely and frequently used in the clinic. However, the development of resistance to β-lactam antibiotics by various pathogens severely has had a damaging effect on maintaining the effective treatment of bacterial infections. The most significant known mechanism related to the development of bacterial resistance is the production of class A, C, and D β-lactamases having a serine residue at the active center. These enzymes decompose the β-lactam antibiotic, resulting in the loss of the antimicrobial activities. Class A β-lactamases preferentially hydrolyze penicillins while class C β-lactamases have a substrate profile favoring cephalosporins. As commercially available β-lactamase inhibitors, clavulanic acid, sulbactam, and tazobactam are known, and these inhibitors are effective mainly against class A β-lactamase producing bacteria, and used as a mixture with a penicillin antibiotic. However, 250 types or more of β-lactamases have been reported to date, and among them, in addition to the expansion of class C β-lactamases as well as extended-spectrum β-lactamase (ESBL) belonging to class A and D β-lactamases, further resistant bacteria which produce class A KPC-2 β-lactamase decomposing even carbapenem as a last resort for β-lactam antibiotic is being considered as a problem. Although the development of a novel inhibitor is strongly demanded as the commercially available inhibitors are ineffective against these β-lactamases and potential inhibitors are disclosed, there are only a few candidates under development.
In recent years, U.S. Pat. No. 7,112,592 (patent document 1) and U.S. Pat. No. 7,612,087 (patent document 2) have disclosed that a racemic diazabicyclooctane derivative is a promising compound in the treatment of an infectious disease as a non-β-lactam antimicrobial or β-lactamase inhibitor, and have demonstrated the working Example of a racemic diazabicyclooctane derivatives from a racemic cis-5-hydroxypiperidine-2-carboxylic acid derivative and those biological activity.
With respect to the optically active diazabicyclooctane derivative, in working Example 1 of WO2009/091856 A2 (patent document 3) and WO2010/126820 A2 (patent document 4), a process for preparing a derivative having a specific amide side chain is described. Further, working Example 1 of patent document 3 has merely a description of a chemical name of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid as an intermediate for research, and similarly, in WO2009/133442 A1 (patent document 5), a chemical name of (2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide is described, and in EP 2135959 A1 (patent document 6), a chemical name of (2S,5R)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide, 7-oxo-6-(sulfoxy)-monosodium salt is described.
On the other hand, with respect to (2S,5S)-5-hydroxypiperidine-2-carboxylic acid and (2S,5R)-5-(benzyloxyamino)piperidine-2-carboxylic acid, which are considered as an important starting material of the diazabicyclooctane derivative, and derivatives thereof, one having an ester side chain has been reported in Tetrahedron Asymmetry 2006, 17(17), 2479-2486 (non-patent document 2) and J. Chem. Soc., Chem. Commun., 1993, 1434 (non-patent document 3), and one having an amide side chain has been reported in working Example 1C of patent document 3, Org. Lett., 2009, 11(16), 3566-3569 (non-patent document 3), and patent document 4. Further, as a process for preparing a derivative not through a (2S,5S)-5-hydroxypiperidine-2-carboxylic acid derivative, US 2010/197928 A (patent document 7) discloses a process for preparing benzyl (2S)-5-(benzyloxyimino)piperidine-2-carboxylate or benzyl (2S,5R/S)-5-(benzyloxyamino)piperidine-2-carboxylare.    [Patent document 1] U.S. Pat. No. 7,112,592    [Patent document 2] U.S. Pat. No. 7,612,087    [Patent document 3] International Publication No. 2009/091856 A2    [Patent document 4] International Publication No. 2010/126820 A2    [Patent document 5] International Publication No. 2009/133442 A1    [Patent document 6] European Patent Application Publication No. 2135959 A1    [Patent document 7] U.S. Patent Application Publication No. 2010/197928 A1    [Non-patent document 1] Jung, J C.; Avery, M A. “Diastereoselective synthesis of (2S,5S)— and (2S,5R)—N-benzyloxycarbonyl-5-hydroxypipecolic acids from trans-4-hydroxy-L-proline” Tetrahedron Asymmetry 2006, 17(17), 2479-2486.    [Non-patent document 2] Baldwin, J E.; Adlington, R M.; Godfrey, C R A.; Gollins, D W.; Vaughan, J G. “A Novel Entry to Carbenoid Species via β-Ketosulfoxonium Ylides” Journal of the Chemical Society Chemical Communications 1993, 1434-1435.    [Non-patent document 3] Mangion, I K.; Nwamba, I K.; Shevlin, M.; Huffman M A. “Iridium-Catalyzed X—H Insertions of Sulfoxonium Ylides” Organic Letters 2009, 11(16), 3566-3569.    [Non-patent document 4] Dolence, E K.; Lin, C E.; Miller, M J.; Payne, S M. “Synthesis and siderophore activity of albomycin-like peptides derived from N5-acetyl-N5-hydroxy-L-ornithine” Journal of Medicinal Chemistry 1991, 34(3), 956-968.    [Non-patent document 5] King, F E.; King, T J.; Warwick, A J. “The Chemistry of Extractives from Hardwoods. Part III. Baikiain, an Amino-acid Present in Baikiaea plurijuga” Journal of the Chemical Society 1950, 3590-3597.    [Non-patent document 6] Witkop, B.; Folts, C M. “The Configuration of 5-Hydroxypipecolic Acid from Dates” Journal of the American Chemical Society 1957, 79(1), 192-197.    [Non-patent document 7] Freed, M E.; Day A R. “Synthesis of 5-Ketopipecolic Acid from Glutamic Acid” The Journal of Organic Chemistry 1960, 25(12), 2105-2107.